It’s About Damn Time

Key Concepts

Those from underrepresented groups are actually underestimated

“I knew when I saw those statistics that the mythology around Silicon Valley was basically a lie, because ingenuity, hard work, hustle, grit, and innovation aren’t traits that are prevalent only in the straight White male population.” (p. 5)

“Just as with stocks, companies, or horses, betting on the people everyone else is betting on is not often the savviest way to do things. In fact, it can be quite lucrative to bet on the underdog. That was the thesis behind my blog post ‘Dear White Venture Capitalists: If You’re Reading This, It’s (Almost!) Too Late.’ I wanted to turn the idea of pattern matching for ‘White male nerds’ on its head and instead use pattern matching to my advantage; I was looking for people who reminded me of myself.” (p. 9)

“I came to realize that women founders, LGBTQ founders, and founders of color aren’t just underrepresented, they are underestimated—a phrase coined and gifted to me by one of the founders I’ve invested in (and wordsmith!) K. G. Harris, during my fund Backstage Capital’s two-year anniversary event in San Francisco.” (p. 14)

It’s all about relationships

“I have not met, seen, or heard about one single solitary founder, executive, leader, or successful person in the history of the world who has done everything on their own. The idea of the self-made person is romantic and perhaps helps some people to strive and push themselves to do more, but overall I find it to be a damaging myth. It encourages the idea of the lone genius, the outlier, and can create an impossible standard to try to live up to.” (p. 43)

“When you don’t have many resources, networks and relationships can be valuable currency. Relationships are one-on-one; networks are how you tie relationships together, and understanding how to navigate both is an important skill.” (p. 52)

“Relationships matter more than money, more than status, more than material things. In any given situation, what makes an experience good or bad is the people involved and your relationship to them. It’s impossible to overstate the value of keeping relationships healthy and treating people well.” (p. 54)

“Write your own headlines”

“Writing my own headlines is something I’ve been doing for several years in one form or another. Think of it as a pocket-sized vision board. I wrote the headline in 2015, and in the years that followed, every time I looked into my draft folder, I saw it staring back at me. It was a reminder of what I was aiming for and something that helped to keep me on track with my goals.” (p. 47)

“This way of planning for the future and setting goals has helped me create a target that is achievable and clearly defined, rather than a collection of vague wishes. Writing your own headlines is a great way of getting closer to making your own headlines.” (p. 48)

Valuing yourself

“This is another example of my not really understanding unit economics back then, because I should have made a lot of money from it. But I tended to undercut myself, undersell myself, and not charge the right amount. I had the best intentions, a product people loved, a loyal fan base, but I would run out of capital or not optimize for profit because I didn’t know any better.” (p. 94)

“So when I say, ‘be the money,’ that means know your numbers, do your market research, make sure your unit economics work and make sense, all of that. I am saying it from a place of wanting you not to repeat the mistakes I’ve made. Talk to people who have been there, done that, before attempting something new. It’s always worth the time investment.” (p. 94)

“Some years ago, I started asking for what I’m worth and accepting nothing less. A funny thing happened: I started getting it. You have to be prepared for those who say no. But as long as you’re willing to walk away when that happens, people who understand your true value will come along.” (p. 173)

“No matter how you make a living or what your skill set is, you have to know what value you bring, place a price on your time and talent, and then accept nothing less.” (p. 176)

Being agile and resilient

“Over the years, I’ve learned how to adapt very quickly, to compartmentalize to protect myself, and how to separate the personal from the professional. This is not something that you learn once and you are great at it forever. You have to work on this as you would a muscle. You have to work on this as a craft. You have to be able to take in what has happened, accept it as reality, and convince yourself that it will be okay, that it is not the end, because a lot of these bigger moments can feel like everything in the moment.” (p. 100)

“Silicon Valley Bank economist Natalie Fratto has coined the term ‘adaptability quotient’ (AQ) to go along with the better-known intelligence quotient (IQ) and emotional quotient (EQ).” (p. 101)

“Repurposing fear into energy and excitement, repurposing anger into action. Something that has made the most impact on me is realizing that forgiveness is the ultimate productivity hack.” (p. 103)

“But there has to be something that kicks in, a different gear that you shift into when you are incredibly disappointed and when life hands you circumstances that are seemingly overwhelming. You have to turn a gear inside you that enables you to take one more step forward and not get lost and buried in your own sorrow.” (p. 103)

“Write Your Own Invitation”

“There have been many times in my life when I could have just given up on something because it wasn’t easy or because it wasn’t clear how I could make it happen. Difficult situations often look like impossible situations until you see the little chink in the armor, the back route, the work-around. Over the years, I’ve realized that there is almost always a work-around.” (p. 145)

“When you’re underestimated, you’re less likely to receive an invitation to the party. You don’t have the same “ins” that other people have. Maybe you don’t have the money or you don’t have the contacts, but that doesn’t mean you don’t deserve to be there. Sometimes you have to write your own invitation. Pull your own chair up to the table. Scribble your own name on the VIP list, and don’t let anyone tell you that you don’t belong.” (p. 148)

Self-Care

“My approach when facing big decisions in business or working on major strategy for Backstage and beyond is the same as my approach to dealing with personal decisions. It’s the same formula I used five years ago, when I was broke: I read, I rest my body and my mind, I reflect and regroup; then I repeat.” (p. 182)

“You will always waste more time if you don’t use it strategically, and taking a break to think and reflect is always a strategic use of time.” (p. 182)

“Caring for yourself has positive effects on all aspects of your life. Though spending eighteen hours a day working on a project can feel as though it will lead to a better product at the end of the day, it can often have the opposite effect. Taking a step away from a project can enable you to see it with fresh eyes.” (p. 193)

Quotables

“Ascending an escalator in a hotel I couldn’t afford to stay in, I said to myself, ‘You are a venture capitalist. You are a venture capitalist.’ I had no home, no money, certainly no investment capital, yet I knew that was what I needed to say to myself. In order to become, I needed to be.” (p. 3)Self-belief alone will not achieve your goals, but achieving your goals without self-belief will be almost impossible. (p. 17)

“I’m asked all the time: ‘How do I know whether or not I should keep going or give up on this company or this project or this mission?’ My answer is this: If you close your eyes and visualize the world five, ten, twenty years from now and feel okay with the thing you’re working on not existing, then it’s not urgent. But if you can’t imagine the world without it and want it to exist whether you get to enjoy the benefits of it or not, then not only is it important to you, it is your calling.” (p. 12)

“I believe that if you have no assets, you have to become the asset. You must become not just valuable but undeniably invaluable. And the way to do that is through having more knowledge about your corner of the world than anyone else.” (p. 25)

“When the majority of the world looks at you as ‘other,’ it becomes imperative to connect with people who have the ability to see you as you—people who are the same as you in some way, whose first impressions of you don’t stem from assumptions regarding race, gender, or sexuality.” (p. 56)

“This is something I would recommend to everyone; use the energy that anger gives you to create something new or to get your house in order. Repurpose it. The next time you feel as though everything is broken, as though you have nothing to give, get creative.” (p. 91)

“I’ve found, both throughout my career and in my personal life, that authenticity is of the utmost importance. Anytime I’ve tried to stray away from who I am, it’s come back to haunt me. Being 100 percent yourself is simultaneously the easiest and the hardest thing you can do.” (p. 11)

“Someone right now is looking for you; someone is looking for a person who reminds them of herself and makes her feel comfortable. Right now, you as you are, your authentic self, you are that person. And if you put on a costume, she’s going to walk right by you.” (p. 138)

“Whenever I doubt myself or I worry that I might be overstepping or thinking too big, I ask myself, ‘What would a White male do?’ That usually snaps me right out of it! If it’s an idea he would pitch, if it’s a question he would ask without embarrassment, if it’s a move he would make, there’s no reason I shouldn’t do the same.” (p. 163)

“I am often asked: How should I invest my money? Which companies are going to give me the best return? What’s the best bet for me? My answer is simple: You are your best bet.” (p. 197)

“That Fast Company cover article described me as part of the ‘new guard.’ Soon after, someone on Twitter wrote that instead of thinking of me as a new type of gatekeeper, people should think of me as a key maker. I loved that and couldn’t agree more. Being a key maker is all about understanding your privilege and sharing it to lift others up.” (p. 211)